TWI769354B - Organic metal compound and organic light-emitting device - Google Patents

Abstract

Organic metal compounds, and organic light-emitting devices employing the same are provided. The organic metal compound has a chemical structure of Formula (I) or Formula (II):

, wherein one of following two conditions (1) and (2) is met: (1) R¹ is deuterium or C_1-6 deuterated alkyl group, when R³ and R⁴ are independently hydrogen, halogen, C_1-6 alkyl group, C_1-6 fluoroalkyl or C_3-12 heteroaryl group; and (2) R¹ is hydrogen, deuterium, C_1-6 alkyl group, C_1-6 deuterated alkyl group, C_3-12 heteroaryl group, or C_6-12 aryl group, when at least one of R³ and R⁴ is C_6-12 aryl group or C_6-12 fluoroaryl group.

Description

Organometallic compound and organic light-emitting device comprising the same

The present disclosure relates to an organometallic compound and an organic light-emitting device including the same.

An organic electroluminescent device (organic electroluminescent device), also known as an organic light-emitting diode (OLED), is a light-emitting diode (LED) with an organic layer as an active layer. Due to the advantages of low voltage operation, high brightness, light weight, wide viewing angle, and high contrast ratio, organic electroluminescent devices have been gradually used in flat panel displays in recent years. Different from the liquid crystal display, the organic light emitting diode pixel array included in the organic electroluminescent display has the characteristic of self-luminescence, so no external backlight is required.

In general, an organic light emitting diode device includes a pair of electrodes, and an organic light emitting medium layer between the electrodes. Light emission is caused by the following phenomenon. When an electric field is applied to the two electrodes, the cathode emits electrons to the organic light-emitting medium layer, and the anode emits holes to the organic light-emitting medium layer. When electrons and holes combine in the organic light-emitting medium layer, excitons are generated. The recombination of electrons and holes is accompanied by luminescence.

The excitons generated by the recombination of holes and electrons can have either a triplet or a singlet spin state, depending on the spin state of the hole and the electron. The luminescence generated by the singlet exciton is fluorescence, and the luminescence generated by the triplet exciton is phosphorescence. The luminous efficiency of phosphorescence is three times that of fluorescence. Therefore, the development of high-efficiency phosphorescent materials to improve the luminous efficiency of organic light-emitting diode devices is the trend of the times.

According to an embodiment of the present disclosure, the present disclosure provides an organometallic compound having a structure represented by formula (I) or formula (II):

Wherein, X is O or S; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C 6- 12 aryl, C7-18 alkaryl, or C6-12 fluoroaryl; R ⁶ , R ⁷ and R ⁸ are each independently and are hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, _C3-12 heteroaryl or _C6-12 aryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _{1 -6} deuterated alkyl, C _1-6 fluoroalkyl, or two adjacent R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² and the carbon atoms to which they are bonded respectively form an aryl group, or a cycloalkyl group; R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 fluoroalkyl, or two adjacent R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ and the carbon atom to which each is bonded constitute an aryl group, or a cycloalkyl group.

Wherein, R ¹ , R ³ and R ⁴ meet any one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

According to another embodiment of the present disclosure, the present disclosure provides an organic light emitting device, which includes a pair of electrodes; and a light-emitting unit disposed between the pair of electrodes, wherein the light-emitting unit includes the above-mentioned Organometallic compounds.

In order to make the above-mentioned objects, features and advantages of the present disclosure more obvious and easy to understand, the following embodiments are given and described in detail in conjunction with the accompanying drawings.

10‧‧‧Organic Light Emitting Device

12‧‧‧Substrate

14‧‧‧Lower electrode

16‧‧‧Organic light-emitting unit

18‧‧‧Top electrode

FIG. 1 is a schematic cross-sectional structure diagram of an organic light-emitting device according to an embodiment of the present disclosure.

organometallic compounds

According to an embodiment of the present disclosure, the organometallic compound described in the present disclosure is an iridium metal hexacoordination complex with at least one furopyridine ligand or thienopyridine, and is further matched with a phenylpyridine (phenylpyridine) compound or acetylacetonate compound as a ligand. In addition to good thermal stability and electrochemical stability, the organometallic compounds described in the present disclosure also have appropriate highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (lowest unoccupied molecular orbital). orbital, LUMO) energy levels, which can effectively convert holes and electrons to form excitons and release phosphorescence (light color with green light) to improve the luminous efficiency of organic light-emitting devices. In addition, according to an embodiment of the present disclosure, the furopyridine ligand or thienopyridine ligand of the organometallic compound of the present disclosure can further introduce a biphenyl group to extend the conjugation length , which can effectively improve the lifetime performance and luminous efficiency of the organic light-emitting device. Furthermore, according to an embodiment of the present disclosure, the hydrogen on the carbon of the organometallic compound described in the present disclosure can be further deuterium or deuterated in its furopyridine ligand, thienopyridine ligand, or phenylpyridine ligand. Alkyl substitution increases the thermal stability and electrochemical stability of the organometallic compound, thereby effectively improving the lifespan performance of the organic light-emitting device.

According to an embodiment of the present disclosure, the present disclosure provides an organometallic compound, which may have a structure represented by formula (I) or formula (II):

Wherein, X is O or S; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _{6 -12} aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl; R ⁶ , R ⁷ and R ⁸ are each independently and are hydrogen, deuterium, C _1-6 alkyl, C _{1- 6} deuterated alkyl, C _3-12 heteroaryl or C _6-12 aryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl , C _1-6 deuterated alkyl, C _1-6 fluoroalkyl, or two adjacent R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² and the carbon atoms to which they are bonded respectively form an aryl group, or a cycloalkane R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 fluoroalkyl, or two adjacent R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ and the carbon atom to which each of them is bonded constitute an aryl group or a cycloalkyl group.

Wherein, R ¹ , R ³ and R ⁴ meet any one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

According to an embodiment of the present disclosure, the C _1-6 alkyl group may be a linear or branched chain alkyl group. For example, C _1-6 alkyl can be methyl, ethyl, propyl, isopropyl, n-butyl, tert-butyl ( t-butyl), sec-butyl, isobutyl, pentyl, or hexyl. According to an embodiment of the present disclosure, the halogen may be fluorine, chlorine, bromine, or iodine. According to an embodiment of the present disclosure, C _1-6 fluoroalkyl refers to an alkyl group in which all or part of the hydrogens on carbon are replaced by fluorine, and can be linear or branched, such as fluoromethyl, or fluoroethyl. Here, the fluoromethyl group in the present disclosure can be monofluoromethyl, difluoromethyl, or perfluoromethyl, and the fluoroethyl group can be monofluoroethyl, difluoroethyl, trifluoroethyl, tetrafluoroethyl Fluoroethyl, or perfluoroethyl. According to an embodiment of the present disclosure, the C _1-6 alkoxy group may be a linear or branched chain alkoxy group. For example, C _1-6 alkoxy is methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentyloxy oxy, or hexyloxy. According to an embodiment of the present disclosure, the C _6-12 aryl group may be phenyl, biphenyl, or naphthyl. According to an embodiment of the present disclosure, the C3-12 heteroaryl group may be furyl, imidazolyl, pyridyl, thiazolyl, thienyl group, or triazolyl ( triazolyl). According to an embodiment of the present disclosure, C _1-6 deuterated alkyl refers to an alkyl group in which all or part of the hydrogens on carbon are replaced by deuterium, and can be linear or branched, such as Deuterated methyl, or deuterated ethyl. Here, the deuterated methyl group in the present disclosure can be mono-deuterated methyl group, di-deuterated methyl group, or per-deuterated methyl group, and the deuterated ethyl group can be mono-deuterated ethyl group or di-deuterated ethyl group , tri-deuterated ethyl, tetra-deuterated ethyl, or per-deuterated ethyl. According to an embodiment of the present disclosure, the cycloalkyl group may be cyclopentyl or cyclohexyl. According to an embodiment of the present disclosure, a C _7-18 alkaryl group refers to an aryl group in which all or part of the hydrogen on one carbon is substituted by an alkyl group (eg, a C _1-4 alkyl group). For example, the C _7-18 alkaryl group can be methylphenyl, or dimethylphenyl. According to an embodiment of the present disclosure, the C _6-12 fluoroaryl group refers to an aryl group in which all or part of the hydrogen on one carbon is replaced by fluorine, such as a fluorophenyl group. Here, the fluorophenyl group of the present disclosure may be monofluorophenyl group, difluorophenyl group, trifluorophenyl group, tetrafluorophenyl group, or perfluorophenyl group.

According to an embodiment of the present disclosure, R ¹ can be hydrogen, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, deuterium, deuterium methyl, deuterated ethyl, phenyl, biphenyl, naphthyl, furyl, imidazolyl, pyridyl, thiazolyl, thienyl, or triazolyl. According to an embodiment of the present disclosure, R ² , R ³ , R ⁴ , and R ⁵ can be independently hydrogen, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl , tert-butyl, pentyl, hexyl, fluoromethyl, fluoroethyl, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-Butoxy, pentyloxy, hexyloxy, phenyl, biphenyl, naphthyl, furyl, imidazolyl, pyridyl, thiazolyl, thienyl, triazolyl, methylphenyl, or fluorobenzene base. According to embodiments of the present disclosure, R ⁶ , R ⁷ , and R ⁸ can be independently hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl yl, pentyl, hexyl, deuterated methyl, or deuterated ethyl, phenyl, biphenyl, naphthyl, furyl, imidazolyl, pyridyl, thiazolyl, thienyl, or triazolyl. According to embodiments of the present disclosure, R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² can be independently hydrogen, fluorine, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isopropyl Butyl, tert-butyl, pentyl, hexyl, deuterated methyl, or deuterated ethyl, fluoromethyl, or fluoroethyl. According to an embodiment of the present disclosure, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ can be independently hydrogen, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl , tert-butyl, pentyl, hexyl, fluoromethyl, or fluoroethyl.

According to an embodiment of the present disclosure, when R ³ and R ⁴ are independently hydrogen, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl , hexyl, fluoromethyl, fluoroethyl, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, pentoxy group, hexyloxy, furanyl, imidazolyl, pyridyl, thiazolyl, thienyl, or triazolyl (that is, when both R ³ and R ⁴ are not C _6-12 aryl, C _7-18 alkane group, or C _6-12 fluoroaryl group), R ¹ is deuterium, deuterated methyl, or deuterated ethyl. According to the embodiments of the present application, when R ¹ of the organometallic compound having the structure represented by formula (I) or formula (II) in the present disclosure is deuterium, deuterated methyl, or deuterated ethyl (ie, furo When the hydrogen on the carbon atom next to the oxygen atom of the furopyridine group is replaced by deuterium, deuterated methyl, or deuterated ethyl; or the carbon atom next to the sulfur atom of the thienopyridine group When hydrogen is replaced by deuterium, deuterated methyl, or deuterated ethyl), the electrochemical stability and thermal stability of the organometallic compound can be greatly increased. In this way, the lifetime performance of the organic light-emitting device can be effectively improved.

According to an embodiment of the present disclosure, when at least one of R ³ and R ⁴ is phenyl, biphenyl, naphthyl, methylphenyl, dimethylphenyl, or fluorophenyl, R ¹ is hydrogen, deuterium, Methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, deuterated methyl, deuterated ethyl, phenyl, biphenyl yl, naphthyl, furyl, imidazolyl, pyridyl, thiazolyl, thienyl, or triazolyl. According to the embodiments of the present application, when the organometallic compound having the structure represented by formula (I) or formula (II) described in the present disclosure, at least one of R ³ and R ⁴ is phenyl, biphenyl, naphthyl, methyl In the case of a phenyl group, a dimethylphenyl group, or a fluorophenyl group, in this case, the furopyridine ligand or the thienopyridine ligand has a biphenyl group. In this way, the conjugation length of the furanopyridine or the thienopyridine can be extended, and the lifetime performance and luminous efficiency of the organic light-emitting device can be effectively improved. According to an embodiment of the present disclosure, when one of R ³ and R ⁴ is phenyl, biphenyl, naphthyl, methylphenyl, dimethylphenyl, or fluorophenyl, the other may be hydrogen, or fluorine.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、 C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；以及，R⁶、R⁷及R⁸係各自獨立且為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。其中，R¹、R³、及R⁴係符合以下(1)-(2)條件之一者：(1)當R³及R⁴獨立為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、或C_3-12雜芳基時，R¹為氘或C_1-6氘代烷基；或(2)當R³及R⁴至少一者為C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基時，R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound is

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl; and, R ⁶ , R ⁷ and R ⁸ are each independently and are hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl. Wherein, R ¹ , R ³ , and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；以及，R⁶、R⁷及R⁸係各自獨立且為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound may be

R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl group, C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl; and, R ⁶ , R ⁷ and R ⁸ are each independently and are hydrogen, deuterium, C _1-6 Alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or C _6-12 aryl.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；R⁶、R⁷及R⁸係各自獨立且為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；以及，R¹⁷、R¹⁸、R¹⁹、R²⁰、及R²¹係各自獨立且為氫、氟、或甲基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl; R ⁶ , R ⁷ and R ⁸ are each independently and are hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or _C6-12 aryl; and, R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , and R ²¹ are each independently and are hydrogen, fluorine, or methyl.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基。其中，R¹、R³、及R⁴係符合以下(1)-(2)條件之一者：(1)當R³及R⁴獨立為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、或C_3-12雜芳基時，R¹為氘或C_1-6氘代烷基；或(2)當R³及R⁴至少一者為C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基時，R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl. Wherein, R ¹ , R ³ , and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；以及，R⁶、R⁷及R⁸係各自獨立且為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。其中，R¹、R³、及R⁴係符合以下(1)-(2)條件之一者：(1)當R³及R⁴獨立為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、或C_3-12雜芳基時，R¹為氘或C_1-6氘代烷基；或(2)當R³及R⁴至少一者為C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基時，R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl; and, R ⁶ , R ⁷ and R ⁸ are each independently and are hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl. Wherein, R ¹ , R ³ , and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12 氟代芳基；以及，R⁶、R⁷及R⁸係各自獨立且為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound may be

R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl group, C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl; and, R ⁶ , R ⁷ and R ⁸ are each independently and are hydrogen, deuterium, C _1-6 Alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or C _6-12 aryl.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；R⁶、R⁷及R⁸係各自獨立且為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；以及，R¹⁷、R¹⁸、R¹⁹、R²⁰、及R²¹係各自獨立且為氫、氟、或甲基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl; R ⁶ , R ⁷ and R ⁸ are each independently and are hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or _C6-12 aryl; and, R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , and R ²¹ are each independently and are hydrogen, fluorine, or methyl.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基。其中，R¹、R³、及R⁴係符合以下(1)-(2)條件之一者：(1)當R³及R⁴獨立為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、或C_3-12雜芳基時，R¹為氘或C_1-6氘代烷基；或(2)當R³及R⁴至少一者為C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基時，R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl. Wherein, R ¹ , R ³ , and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；R⁹、R¹⁰、R¹¹、及R¹²係各自獨立且為氫、鹵素、氘、C_1-6烷基、C_1-6氘代烷基、C_1-6氟烷基、或兩相鄰的R⁹、R¹⁰、R¹¹、及R¹²與其各自鍵結的碳原子構成一芳香基、或環烷基；以及，R¹³、R¹⁴、R¹⁵、及R¹⁶係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6氟烷基、或兩相鄰的R¹³、R¹⁴、R¹⁵、及R¹⁶與其各自鍵結的碳原子構成一芳香基、或環烷基。其中，R¹、R³、及R⁴係符合以下(1)-(2)條件之一者：(1)當R³及R⁴獨立為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、或C_3-12雜芳基時，R¹為氘或C_1-6氘代烷基；或(2)當R³及R⁴至少一者為C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基時，R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _1-6 Deuterated alkyl, C _1-6 fluoroalkyl, or two adjacent R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² and the carbon atoms to which they are bonded respectively form an aryl group, or a cycloalkyl group; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 fluoroalkyl, or two adjacent R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ and the carbon atom to which each is bonded constitute an aryl group, or a cycloalkyl group. Wherein, R ¹ , R ³ , and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；R⁹、R¹⁰、R¹¹、及R¹²係各自獨立且為氫、鹵素、氘、C_1-6烷基、C_1-6氘代烷基、C_1-6氟烷基、或兩相鄰的R⁹、R¹⁰、R¹¹、及R¹²與其各自鍵結的碳原子構成一芳香基、或環烷基；以及，R¹³、R¹⁴、R¹⁵、及R¹⁶係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6氟烷基、或兩相鄰的R¹³、R¹⁴、R¹⁵、及R¹⁶與其各自鍵結的碳原子構成一芳香基、或環烷基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 hetero Aryl, C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium , C _1-6 alkyl, C _1-6 deuterated alkyl, C _1-6 fluoroalkyl, or two adjacent carbon atoms of R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² and their respective bonding an aryl, or cycloalkyl; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 fluoroalkyl, or biphasic Adjacent R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ and the carbon atom to which each of them is bonded constitute an aryl group or a cycloalkyl group.

或

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基。其中，R¹、R³、及R⁴係符合以下(1)-(2)條件之一者：(1)當R³及R⁴獨立為氫、 鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、或C_3-12雜芳基時，R¹為氘或C_1-6氘代烷基；或(2)當R³及R⁴至少一者為C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基時，R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound may be

or

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl. Wherein, R ¹ , R ³ , and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；R⁹、R¹⁰、R¹¹、及R¹²係各自獨立且為氫、鹵素、氘、C_1-6烷基、C_1-6氘代烷基、C_1-6氟烷基、或兩相鄰的R⁹、R¹⁰、R¹¹、及R¹²與其各自鍵結的碳原子構成一芳香基、或環烷基；以及，R¹³、R¹⁴、R¹⁵、及R¹⁶係各自 獨立且為氫、鹵素、C_1-6烷基、C_1-6氟烷基、或兩相鄰的R¹³、R¹⁴、R¹⁵、及R¹⁶與其各自鍵結的碳原子構成一芳香基、或環烷基；以及，R¹⁷、R¹⁸、R¹⁹、R²⁰、及R²¹係各自獨立且為氫、氟、或甲基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _1-6 Deuterated alkyl, C _1-6 fluoroalkyl, or two adjacent R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² and the carbon atoms to which they are bonded respectively form an aryl group, or a cycloalkyl group; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 fluoroalkyl, or two adjacent R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ and the carbon atom to which each is bonded constitute an aryl group, or a cycloalkyl group; and, R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , and R ²¹ are each independently and are hydrogen, fluorine, or methyl.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；R⁹、R¹⁰、R¹¹、及R¹²係各自獨立且為氫、鹵素、氘、C_1-6烷基、C_1-6氘代烷基、C_1-6氟烷基、或兩相鄰的R⁹、R¹⁰、R¹¹、及R¹²與其各自鍵結的碳原子構成一芳香基、或環烷基；以及，R¹³、R¹⁴、R¹⁵、及R¹⁶係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6氟烷基、或兩相鄰的R¹³、R¹⁴、R¹⁵、及R¹⁶與其各自鍵結的碳原子構成一芳香基、或環烷基。其中，R¹、R³、及R⁴係符合以下(1)-(2)條件之一者：(1)當R³及R⁴獨立為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、或C_3-12雜芳基時，R¹為氘或C_1-6氘代烷基；或(2)當R³及R⁴至少一者為C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基時，R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _1-6 Deuterated alkyl, C _1-6 fluoroalkyl, or two adjacent R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² and the carbon atoms to which they are bonded respectively form an aryl group, or a cycloalkyl group; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 fluoroalkyl, or two adjacent R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ and the carbon atom to which each is bonded constitute an aryl group, or a cycloalkyl group. Wherein, R ¹ , R ³ , and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；R⁹、R¹⁰、R¹¹、及R¹²係各自獨立且為氫、鹵素、氘、C_1-6烷基、C_1-6氘代烷基、C_1-6氟烷基、或兩相鄰的R⁹、R¹⁰、R¹¹、及R¹²與其各自鍵結的碳原子構成一芳香基、或環烷基；以及，R¹³、R¹⁴、R¹⁵、及R¹⁶係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6氟烷基、或兩相鄰的R¹³、R¹⁴、R¹⁵、及R¹⁶與其各自鍵結的碳原子構成一芳香基、或環烷基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 hetero Aryl, C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium , C _1-6 alkyl, C _1-6 deuterated alkyl, C _1-6 fluoroalkyl, or two adjacent carbon atoms of R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² and their respective bonding an aryl, or cycloalkyl; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 fluoroalkyl, or biphasic Adjacent R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ and the carbon atom to which each of them is bonded constitute an aryl group or a cycloalkyl group.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基。其中，R¹、R³、及R⁴係符合以下(1)-(2)條件之一者：(1)當R³及R⁴獨立為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、或C_3-12雜芳基時，R¹為氘或C_1-6氘代烷基；或(2)當R³及R⁴至少一者為C_6-12芳香基、C_7-18烷 芳基、或C_6-12氟代芳基時，R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl. Wherein, R ¹ , R ³ , and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy, C _1-6 fluoroalkyl, or C _3-12 heteroaryl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl.

；R¹為氫、氘、C_1-6烷基、C_1-6氘代烷基、C_3-12雜芳基或C_6-12芳香基；R²、R³、R⁴、及R⁵係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6烷氧基、C_1-6氟烷基、C_3-12雜芳基、C_6-12芳香基、C_7-18烷芳基、或C_6-12氟代芳基；R⁹、R¹⁰、R¹¹、及R¹²係各自獨立且為氫、鹵素、氘、C_1-6烷基、C_1-6氘代烷基、C_1-6氟烷基、或兩相鄰的R⁹、R¹⁰、R¹¹、及R¹²與其各自鍵結的碳原子構成一芳香基、或環烷基；R¹³、R¹⁴、R¹⁵、及R¹⁶係各自獨立且為氫、鹵素、C_1-6烷基、C_1-6氟烷基、或兩相鄰的R¹³、R¹⁴、R¹⁵、及 R¹⁶與其各自鍵結的碳原子構成一芳香基、或環烷基；以及，R¹⁷、R¹⁸、R¹⁹、R²⁰、及R²¹係各自獨立且為氫、氟、或甲基。 According to an embodiment of the present disclosure, the organometallic compound may be

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _3-12 heteroaryl, C _6-12 aryl, C _{7 -18} alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _1-6 Deuterated alkyl, C _1-6 fluoroalkyl, or two adjacent R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² and the carbon atoms to which they are bonded respectively form an aryl group, or a cycloalkyl group; R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 fluoroalkyl, or two adjacent R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ The carbon atom to which each is bonded constitutes an aryl group, or a cycloalkyl group; and, R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , and R ²¹ are each independently and are hydrogen, fluorine, or methyl.

The organometallic compounds having the structures of formula (I) and formula (II) according to the present invention have at least one furopyridine ligand or thienopyridine, and a phenylpyridine compound or Acetylacetone (acetylacetonate) ligand. The furopyridine ligand or thienopyridine ligand of the organometallic compound of the present disclosure can further introduce a biphenyl group to extend the conjugation length, which can effectively improve the performance of organic light-emitting devices. Lifetime performance and luminous efficiency. On the other hand, according to an embodiment of the present disclosure, the hydrogen on the carbon of the organometallic compound of the present disclosure can be further deuterium or deuterium. Substituted with an alkyl group to increase the thermal stability and electrochemical stability of the organometallic compound, thereby effectively improving the lifetime performance of the organic light-emitting device.

Table 1 series lists the organometallic compounds having the structure represented by formula (I) obtained in the embodiments of the present disclosure, and shows the chemical structure and the strongest luminescence peak (Emission λ _max ) of the photoluminescence (PL) spectrum.

In addition, Table 2 series lists the organometallic compounds having the structure represented by formula (II) obtained in the embodiments of the present disclosure, and shows the chemical structure and the strongest luminescence peak (Emission _λmax ) of the photoluminescence (PL) spectrum. ).

The photoluminescence (PL) spectrum of the organometallic compound described in the present disclosure is measured by dissolving the organometallic compound in dichloromethane (with a weight percent concentration of 10 ^-5 M). As can be seen from Table 1 and Table 2, the organometallic compounds having the structures represented by formula (I) and formula (II) described in the present disclosure have the strongest emission peaks ranging from 529 nm to 573 nm (belonging to green phosphorescent materials).

In order to further illustrate the preparation methods of the organometallic compounds described in the present disclosure, the preparation processes of the organometallic compounds described in Examples 1-4, 6, 7, 11, and 15-22 are described below.

Preparation of Organometallic Compounds (I)

Furan-2-carbaldehyde (48g, 500mmol), malonic acid (78.04g, 750mmol), pyridine (23g), and a catalytic amount of piperidine were added to a reaction bottle and heated to reflux (about 90°C) under nitrogen. After 3 hours of reaction, the resultant was added with methanol (100 ml), and it was lowered to room temperature. After sufficient stirring, the resultant was poured into water, and the compound (1) (Compound (1)) was obtained after precipitation and filtration. The reaction formula of the above reaction is as follows:

Next, compound (1) (55.93 g, 405 mmol) and dichloromethane (DCM) (405 ml) were added to a reaction flask. Next, oxalyl chloride (66.7 g, 526 mmol) was slowly added dropwise. When the ethylene glycol chloride was completely added, a catalytic amount of dimethylformamide (DMF) was added to the reaction flask. After 2 hours of reaction at room temperature, vacuum was applied to completely remove the solvent, and acetone was added to the reaction vial. After cooling to 0°C, an aqueous solution of sodium azide (NaN ₃ ) (52.6 g, 809 mmol) was added to the reaction flask. After 16 hours of reaction, water was added to the reaction flask. After filtration, compound (2) was obtained (Compound (2)). The reaction formula of the above reaction is as follows:

Next, n-tributylamine ((nBu) ₃ N) (41.3 ml, 500 mmol) and diphenyl ether (21.7 ml) were added to a reaction flask. Next, the reaction flask was heated to 230° C., and compound (2) (40.8 g, 250 mmol) (dissolved in 217 ml of diphenyl ether) was slowly dropped into the reaction flask. After half an hour of reaction, n-hexane was added, and the solid was obtained after precipitation and filtration to obtain compound (3) (Compound (3)). The reaction formula of the above reaction is as follows:

Next, compound (3) (60.0 g, 444 mmol) and phosphorus oxychloride (POCl ₃ ) (62 mL, 666 mmol) were added to a reaction flask, and the reaction flask was heated to 120-140 °C. After 2.5 hours of reaction, the reaction flask was cooled to 25°C, and the reaction was stopped by adding water in an ice bath. Next, sodium hydroxide was added for neutralization, and extracted with ethyl acetate and water, and the organic layer was collected. Next, after removing water and concentrating, it was purified by column chromatography to obtain Compound (4) (Compound (4)). The reaction formula of the above reaction is as follows:

Next, compound (4) (3.52 g, 23.0 mmol), 3-diphenylboronic acid (5.0 g, 25.2 mmol), bis(dibenzylideneacetone)palladium, Pd(dba) ₂ ) (66.0 mg, 0.11 mmol), tri-tert-butylphosphine tetrafluoroborate (tri-tert-butylphosphine tetrafluoroborate, [P(tBu) ₃ ]HBF ₄ ) (67.0 mg, 0.23 mmol), sodium bicarbonate (9.7 g, 91.7 mmol), ethanol (36 ml) and water (12 ml) were added to a reaction flask, and the reaction flask was heated to reflux for 18 hours. Next, after cooling down the reaction flask to room temperature, the resultant was purified by column chromatography to obtain Compound (5) (Compound (5)). The reaction formula of the above reaction is as follows:

Next, compound (5) (1 g, 3.69 mmol), iridium trichloride (IrCl ₃ ) (550 mg, 1.84 mmol), 2-methoxyethanol (15 ml), and water ( 5ml) was added to a reaction flask. Next, after dehydration and oxygen drying, the reaction was heated to reflux under nitrogen atmosphere. After 24 hours of reaction, the reaction was returned to room temperature, water was added for precipitation, the solution was filtered and the solid was washed with water and methanol, the solid was collected and dried under vacuum to obtain compound (6) (Compound (6)). The reaction formula of the above reaction is as follows:

Next, a reaction flask was provided, and compound (6) (1.18g, 0.77mmol), acetylacetone (308mg, 3.07mmol), sodium carbonate (325mg, 3.07mmol), and 2-methoxyethanol ( 2-methoxyethanol) (15ml). Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 130°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (I) (Organic metal compound (I)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (II)

Provide a reaction flask, add compound (7) (Compound (7)) (0.612 mmole), acetylacetone (2.47 mmole), potassium carbonate (2.47 mmole), and 2-methoxyethanol (2-methoxyethanol) ) (6.1 ml). Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 130°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (II) (Organic metal compound (II)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (III)

Provide a reaction flask, add compound (8) (Compound (8)) (0.703 mmole), acetylacetone (2.81 mmole), potassium carbonate (2.81 mmole), and 2-methoxyethanol (2-methoxyethanol) ) (7.0 ml). Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 130°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (III) (Organic metal compound (III)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (IV)

Provide a reaction flask, add compound (9) (Compound (9)) (0.536 mmole), acetylacetone (2.14 mmole), potassium carbonate (2.14 mmole), and 2-methoxyethanol (2-methoxyethanol) ) (7.0 ml). Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 130°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it is purified by column chromatography to obtain an organic metal compound (IV) (Organic metal compound (IV)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (VI)

Provide a reaction flask, add compound (10) (Compound (10)) (0.341 mmole), acetylacetone (2.73 mmole), potassium carbonate (2.73 mmole), and 2-methoxyethanol (2-methoxyethanol) ) (3.5ml). Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 130°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it is purified by column chromatography to obtain an organic metal compound (VI) (Organic metal compound (VI)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (VII)

Provide a reaction flask, add compound (11) (Compound (10)) (1.61 mmole), acetylacetone (6.46 mmole), potassium carbonate (3.22 mmole), and 2-methoxyethanol (2-methoxyethanol) ) (16ml). Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 130°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (VII) (Organic metal compound (VII)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (XI)

2-methyl-6-phenylpyridine (2-methyl-6-phenylpyridine, mPPy) (16.7g, 56.0 mmole), iridium trichloride (iridium trichloride, IrCl ₃ ) (118.0 mmole), 2-methoxy 2-methoxyethanol (420ml), and water (140ml) were added to a reaction flask. Next, after dehydration and oxygen drying, the reaction was heated to reflux under nitrogen atmosphere. After 24 hours of reaction, the reaction was returned to room temperature, water was added for precipitation, the solution was filtered and the solid was washed with water and methanol, the solid was collected and dried under vacuum to give compound (12) (Compound (12)). The reaction formula of the above reaction is as follows:

A reaction flask was provided, and compound (12) (14.2 mmol), and dichloromethane (CH ₂ Cl ₂ ) (142 ml) were added. Provide another reaction flask, add silver trifluoromethanesulfonate (AgOTf) (31.2 mmol) and methanol (156 ml), add this methanol solution to the above dichloromethane solution, and stir at room temperature for 18 hours . After the reaction, the by-product silver chloride was removed by filtration, and the compound (13) (Compound (13)) was obtained after being concentrated and drained. The reaction formula of the above reaction is as follows:

Next, a reaction flask was provided, and compound (13) (11.4 mmol), compound (14) (17.2 mmol), methanol (60 ml), and ethanol (60 ml) were added. Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 90°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (XI) (Organic metal compound (XI)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (XV)

A reaction flask was provided, and compound (13) (1.91 mmol), compound (15) (2.87 mmol), methanol (10 ml), and ethanol (10 ml) were added. Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 90°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (XV) (Organic metal compound (XV)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (XVI)

A reaction flask was provided, and compound (13) (1.80 mmol), compound (16) (2.69 mmol), methanol (9 ml), and ethanol (9 ml) were added. Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 90°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (XVI) (Organic metal compound (XVI)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (XVII)

A reaction flask was provided, and compound (17) (1.35 mmol), compound (15) (2.02 mmol), methanol (8 ml), and ethanol (8 ml) were added. Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 90°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (XVII) (Organic metal compound (XVII)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (XXIII)

A reaction flask was provided, and compound (17) (1.35 mmol), compound (5) (2.02 mmol), methanol (8 ml), and ethanol (8 ml) were added. Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 90°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (XXIII) (Organic metal compound (XXIII)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (XIX)

A reaction flask was provided, and compound (13) (0.80 mmol), compound (18) (1.20 mmol), methanol (4 ml), and ethanol (4 ml) were added. Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 90°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (XIX) (Organic metal compound (XIX)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (XX)

A reaction vial was provided, and compound (13) (0.50 mmol), compound (19) (0.75 mmol), methanol (2.5 ml), and ethanol (2.5 ml) were added. Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 90°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (XX) (Organic metal compound (XX)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (XXI)

A reaction flask was provided, and compound (13) (1.23 mmol), compound (20) (1.84 mmol), methanol (6 ml), and ethanol (6 ml) were added. Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 90°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (XXI) (Organic metal compound (XXI)). The reaction formula of the above reaction is as follows:

Preparation of Organometallic Compounds (XXII)

A reaction flask was provided, and compound (13) (1.59 mmol), compound (21) (1.91 mmol), methanol (8 ml), and ethanol (8 ml) were added. Next, after repeated dehydration and oxygen drying, nitrogen gas was charged, and the reaction was heated to 90°C. After 18 hours of reaction, the reaction was returned to room temperature, water was added to precipitate out, the solution was filtered and the solid was washed with water and n-hexane, the solid was collected and dissolved in dichloromethane (CH ₂ Cl ₂ ). Next, extraction was performed three times with dichloromethane (CH ₂ Cl ₂ ) and water, and the organic layers collected for the three times were dried and filtered, and the product was sucked dry on a cycloconcentrator. Finally, it was purified by column chromatography to obtain an organic metal compound (XXII) (Organic metal compound (XXII)). The reaction formula of the above reaction is as follows:

Next, the organometallic compounds described in Examples 1-22 were analyzed by nuclear magnetic resonance spectroscopy, and the obtained spectral information is shown in Table 3.

organic light emitting device

Please refer to FIG. 1 , which is a schematic cross-sectional structure diagram of an organic light emitting diode (OLED) 10 according to the present disclosure. The organic light emitting device 10 includes a substrate 12 , a lower electrode 14 , and a light-emitting unit 16 and an upper electrode 18 . The organic light-emitting device 10 can be a top-emitting, bottom-emitting, or double-sided light-emitting organic light-emitting device. The substrate can be, for example, glass, a plastic substrate, or a semiconductor substrate. The material of the lower electrode 14 and the upper electrode 18 can be, for example, lithium, magnesium, calcium, aluminum, silver, indium, gold, tungsten, nickel, platinum, copper, indium tin oxide (ITO), indium zinc oxide (IZO) , Zinc Aluminum Oxide (AZO), Zinc Oxide (ZnO) or a combination thereof, and its formation method can be thermal evaporation, sputtering or plasma enhanced chemical vapor deposition. In addition, at least one of the lower electrode 14 and the upper electrode 18 needs to have light-transmitting properties.

The light-emitting unit 16 at least includes a light-emitting layer, and may further include a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer or other layers. It should be noted that, according to the embodiment of the present disclosure, the light-emitting unit 16 must include the organometallic compound having the formula (I) or the formula (II) described in the present disclosure. In other words, in the light-emitting unit 16, at least one film layer includes the organometallic compound described in the present disclosure.

According to another embodiment of the present disclosure, the organic light-emitting device may be a phosphorescent organic light-emitting device (PHOLED), and the light-emitting unit 16 of the phosphorescent organic light-emitting device has a light-emitting layer, and the light-emitting layer includes a A host material and a phosphorescent dopant material, wherein the phosphorescent dopant material comprises the organometallic compound having the structure represented by the formula (I) or the formula (II) described in the present disclosure, and the light-emitting layer emits blue light or blue light green light. Those skilled in the art can dope the organometallic compound described in the present disclosure with the desired phosphorescent dopant material and change the doping of the matched dopant depending on the organic light-emitting material used and the desired device characteristics. quantity. Therefore, the doping amount of the dopant is not a feature of the present disclosure, and is not a basis for limiting the scope of the present disclosure.

To further illustrate the organic light-emitting device of the present disclosure, the following embodiments provide several organic light-emitting device embodiments using the organometallic compounds obtained in the above-mentioned embodiments as doping materials.

Example 23

The patterned indium tin oxide (ITO) (150 nm thick) glass substrates were cleaned by ultrasonic vibration using neutral detergent, acetone and ethanol. Next, the substrate was blown dry with nitrogen, and then UV-OZONE was performed for 30 minutes. Next, ^HATCN (hexaazatriphenylene-hexacarbonitrile, with a thickness of 20 nm), a hole transport material (product code EHT- I-01, sold by Yulei Optoelectronics Technology, thickness is 150nm), electron blocking material (product code is EHT-I-02, sold by Yulei Optoelectronics Technology, thickness is 10nm), light-emitting host material (product code is EPH-I-06, sold by Yulei Optoelectronics Technology) and luminescent co-host material (EPH-I-02, sold by Yulei Optoelectronics Technology) doped with organometallic compound (VIII) (as a dopant) (EPH - The weight ratio of I-06, EPH-I-02 and organometallic compound (VIII) is 56%: 40%: 4%, thickness is 60nm), electron transport material (ETM-785, sold by Yulei Optoelectronics Technology) ) and LiQ (8-hydroxy-quinolinato lithium) (the weight ratio of ETM-785 and LiQ is 1:1, thickness is 30nm), and Al (thickness is 120nm), and organic light emission is obtained after encapsulation Device (I). The structure of the organic light-emitting device (I) can be represented as: ITO/EHT-I-01/EHT-I-02/EPH-I-06: EPH-I-02: Organometallic compound (VIII) /ETM-785: LiQ/Al.

Next, the organic light-emitting device (I) was subjected to voltage, luminance, current efficiency, and lifetime (time required for luminance to decay to 95% of the initial luminance (LT95) and luminance to decay to initial luminance with a luminance meter and a colorimeter. The measurement of the time required for 50% (LT50) (initial brightness is 1000cd/m ² )), please refer to Table 4 for the results.

Example 24

It was carried out in the same manner as in Example 24, except that all of the organometallic compounds (VIII) were replaced by the organometallic compounds (XI) to obtain an organic light-emitting device (II). The structure of the organic light-emitting device (II) can be represented as: ITO/EHT-I-01/EHT-I-02/EPH-I-06: EPH-I-02: Organometallic compound (XI)/ETM-785: LiQ/Al.

Next, the organic light-emitting device (II) was subjected to voltage, luminance, current efficiency, and lifetime (time required for luminance to decay to 95% of the initial luminance (LT95) and luminance to decay to initial luminance with a luminance meter and a colorimeter. The measurement of the time required for 50% (LT50) (initial brightness is 1000cd/m ² )), please refer to Table 4 for the results.

Comparative Example 1

)，得到有機發光裝置(III)。該有機發光裝置(III)之結構可表示為：ITO/EHT-I-01/EHT-I-02/EPH-I-06：EPH-I-02：化合物(22)/ETM-785：LiQ/Al。 The same procedure as in Example 24 was carried out, except that the organometallic compound (VIII) was replaced by the compound (22) (the structure is

) to obtain an organic light-emitting device (III). The structure of the organic light-emitting device (III) can be expressed as: ITO/EHT-I-01/EHT-I-02/EPH-I-06: EPH-I-02: compound (22)/ETM-785: LiQ/ Al.

Next, the organic light-emitting device (III) was subjected to voltage, luminance, current efficiency, and lifetime (time required for luminance to decay to 95% of the initial luminance (LT95) and luminance to decay to initial luminance with a luminance meter and a colorimeter. The measurement of the time required for 50% (LT50) (initial brightness is 1000cd/m ² )), please refer to Table 4 for the results.

It can be seen from Table 4 that, compared with the organic light-emitting device described in Comparative Example 1, the lifetime of the organic light-emitting device described in Examples 23 and 24 can be increased by 2.3 to 7.1 times. This is because the biphenyl group is further introduced into the furopyridine ligands of the organometallic compounds (VIII) and (XI) (compared to the compound (22) used in Comparative Example 1), and the increase The thermal stability and electrochemical stability of the organometallic compounds (VIII) and (XI), thereby improving the lifetime performance of the organic light-emitting device.

Example 25

It was carried out in the same manner as in Example 23, except that the organometallic compound (VIII) was replaced by the organometallic compound (XII) to obtain an organic light-emitting device (IV). The structure of the organic light-emitting device (IV) can be represented as: ITO/EHT-I-01/EHT-I-02/EPH-I-06: EPH-I-02: Organometallic compound (XII)/ETM-785: LiQ/Al.

Next, the organic light-emitting device (IV) was subjected to voltage, luminance, current efficiency, and lifetime (time required for luminance to decay to 95% of the initial luminance (LT95) and luminance to decay to initial luminance with a luminance meter and a colorimeter. The measurement of the time required for 50% (LT50) (initial brightness is 1000cd/m ² )), please refer to Table 5 for the results.

Example 26

It was carried out in the same manner as in Example 23, except that the organometallic compound (VIII) was replaced by the organometallic compound (IX) to obtain an organic light-emitting device (V). The structure of the organic light-emitting device (V) can be represented as: ITO/EHT-I-01/EHT-I-02/EPH-I-06: EPH-I-02: Organometallic compound (IX)/ETM-785: LiQ/Al.

Next, the organic light-emitting device (V) was subjected to voltage, luminance, current efficiency, and lifetime (time required for luminance to decay to 95% of the initial luminance (LT95) and luminance to decay to initial luminance with a luminance meter and a colorimeter. The measurement of the time required for 50% (LT50) (initial brightness is 1000cd/m ² )), please refer to Table 5 for the results.

Example 27

An organic light-emitting device (VI) was obtained in the same manner as in Example 23, except that the organometallic compound (VIII) was replaced by the organometallic compound (X). The structure of the organic light-emitting device (VI) can be represented as: ITO/EHT-I-01/EHT-I-02/EPH-I-06: EPH-I-02: Organometallic compound (X)/ETM-785: LiQ/Al.

Next, the organic light-emitting device (VI) was subjected to voltage, luminance, current efficiency, and lifetime (time required for luminance to decay to 95% of the initial luminance (LT95) and luminance to decay to initial luminance with a luminance meter and a colorimeter. The measurement of the time required for 50% (LT50) (initial brightness is 1000cd/m ² )), please refer to Table 5 for the results.

It can be seen from Table 4 that, compared with the organic light-emitting device described in Example 24, since the organometallic compound used in Example 25 is further introduced into the methyl group of the phenylpyridine ligand with deuterated methyl group, Example 25 is obtained. The lifetime (LT95) of the organic light-emitting device can be increased by 1.59 times. In addition, compared with the organic light-emitting device described in Example 23, since the organometallic compound used in Example 26 is further introduced into the hydrogen of the furopyridine substituted by deuterium, the lifetime (LT95) of the organic light-emitting device described in Example 26 can be improved. 1.78 times. Furthermore, compared with the organic light-emitting device described in Example 26, since the organometallic compound used in Example 27 was further introduced into the methyl group of the phenylpyridine ligand with deuterated methyl group, the organic light-emitting device described in Example 27 was further introduced into the organic light-emitting device described in Example 27. The lifetime of the device (LT95) can be increased by 3.56 times.

Although the present disclosure has been disclosed above with several embodiments, it is not intended to limit the present disclosure. Anyone with ordinary knowledge in the technical field may make any changes and modifications without departing from the spirit and scope of the present disclosure. Therefore, the scope of protection of this disclosure should be determined by the scope of the appended patent application.

10‧‧‧Organic Light Emitting Device

12‧‧‧Substrate

14‧‧‧Lower electrode

16‧‧‧Organic light-emitting unit

18‧‧‧Top electrode

Claims (13)

An organometallic compound having a structure as shown in formula (II):

Wherein, X is O or S; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _6-12 aryl, C _{7- 18} alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _1-6 deuterium substituted alkyl, or C _1-6 fluoroalkyl; R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, or C _1-6 fluoroalkyl, Wherein, R ¹ , R ³ , and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _{1 -6} alkoxy or C _1-6 fluoroalkyl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when at least one of R ³ and R ⁴ is C _6-12 aryl , C _7-18 alkylaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or C _6-12 aryl. The organometallic compound as described in claim 1, wherein when R ³ and R ⁴ are independently hydrogen, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isopropyl Butyl, tert-butyl, pentyl, hexyl, fluoromethyl, fluoroethyl, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy In the case of tert-butoxy, pentyloxy, or hexyloxy, R ¹ is deuterium, deuterated methyl, or deuterated ethyl. The organometallic compound as described in claim 1, wherein at least one of R ³ and R ⁴ is phenyl, biphenyl, naphthyl, methylphenyl, dimethylphenyl, or fluorophenyl When R ¹ is hydrogen, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, deuterated methyl, deuterium ethyl, phenyl, biphenyl, naphthyl, furyl, imidazolyl, pyridyl, thiazolyl, thienyl, or triazolyl. The organometallic compound as described in claim 1, wherein R ² and R ⁵ are independently hydrogen, fluorine, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl , tert-butyl, pentyl, hexyl, fluoromethyl, fluoroethyl, methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy , tert-butoxy, pentyloxy, hexyloxy, phenyl, biphenyl, naphthyl, methylphenyl, or fluorophenyl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are independently hydrogen, Fluorine, deuterium, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, pentyl, hexyl, deuterated methyl, or deuterated ethyl, fluoromethyl, or fluoroethyl; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are independently hydrogen, fluoro, methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl , isobutyl, tert-butyl, pentyl, hexyl, fluoromethyl, or fluoroethyl. The organometallic compound as described in item 1 of the claimed scope, wherein the organometallic compound is

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R The ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, or C _{1 -6} fluoroalkyl; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, or C _1-6 fluoroalkyl, wherein R ¹ , R ³ and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy , or C _1-6 fluoroalkyl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when at least one of R ³ and R ⁴ is C _6-12 aryl, C _7-18 When alkaryl or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or C _6-12 Aromatic group. The organometallic compound as described in item 5 of the claimed scope, wherein the organometallic compound is

or

; R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _6-12 aromatic R ⁹ , R ¹⁰ , R ¹¹ , and R ₁₂ ^are each independently and are hydrogen, halogen, deuterium, C _{1-6 alkyl} , C _1-6 deuterated alkyl, or C _1-6 fluoroalkyl; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, or C _1-6 Fluoroalkyl. The organometallic compound as described in item 5 of the claimed scope, wherein the organometallic compound is

,

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R The ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _6-12 aryl, C _7-18 alkaryl, or C _{6-12 Fluoroaryl} , wherein R ¹ , R ³ , and R ⁴ meet one of the following (1)-(2) conditions: (1) When R ³ and R ⁴ are independently hydrogen, halogen, C When _1-6 alkyl, C _1-6 alkoxy, or C _1-6 fluoroalkyl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when R ³ and R ⁴ are at least one When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl , C _3-12 heteroaryl or C _6-12 aryl. The organometallic compound as described in item 5 of the claimed scope, wherein the organometallic compound is

or

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R The ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, or C _{1 -6} fluoroalkyl; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, or C _1-6 fluoroalkyl; and, R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , and R ²¹ are each independently and are hydrogen, fluorine, or methyl. The organometallic compound as described in item 1 of the claimed scope, wherein the organometallic compound is

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R The ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, or C _{1 -6} fluoroalkyl; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, or C _1-6 fluoroalkyl, wherein R ¹ , R ³ and R ⁴ meet one of the following conditions (1)-(2): (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy , or C _1-6 fluoroalkyl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when at least one of R ³ and R ⁴ is C _6-12 aryl, C _7-18 When alkaryl or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or C _6-12 Aromatic group. The organometallic compound as described in claim 9, wherein the organometallic compound is

or

; R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _6-12 aromatic R ⁹ , R ¹⁰ , R ¹¹ , and R ₁₂ ^are each independently and are hydrogen, halogen, deuterium, C _{1-6 alkyl} , C _1-6 deuterated alkyl, or C _1-6 fluoroalkyl; and, R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, or C _1-6 Fluoroalkyl. The organometallic compound as described in claim 9, wherein the organometallic compound is

,

R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R ⁵ are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _6-12 aryl, C _7-18 alkaryl, or C _{6 -12 Fluoroaryl} , wherein R ¹ , R ³ , and R ⁴ meet one of the following (1)-(2) conditions: (1) When R ³ and R ⁴ are independently hydrogen, halogen, C _{1 -6} alkyl, C _1-6 alkoxy, or C _1-6 fluoroalkyl, R ¹ is deuterium or C _1-6 deuterated alkyl; or (2) when at least one of R ³ and R ⁴ When it is C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl, R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl or C _6-12 aryl. The organometallic compound as described in claim 9, wherein the organometallic compound is

,or

; R ¹ is hydrogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, C _3-12 heteroaryl, or C _6-12 aryl; R ² , R ³ , R ⁴ , and R The ⁵ series are each independently and are hydrogen, halogen, C _1-6 alkyl, C _1-6 alkoxy, C _1-6 fluoroalkyl, C _6-12 aryl, C _7-18 alkaryl, or C _6-12 fluoroaryl; R ⁹ , R ¹⁰ , R ¹¹ , and R ¹² are each independently and are hydrogen, halogen, deuterium, C _1-6 alkyl, C _1-6 deuterated alkyl, or C _{1 -6} fluoroalkyl; R ¹³ , R ¹⁴ , R ¹⁵ , and R ¹⁶ are each independently and are hydrogen, halogen, C _1-6 alkyl, or C _1-6 fluoroalkyl; and, R ¹⁷ , R ¹⁸ , R ¹⁹ , R ²⁰ , and R ²¹ are each independently and are hydrogen, fluorine, or methyl. An organic light-emitting device, comprising: a pair of electrodes; and An organic light-emitting unit is disposed between the pair of electrodes, wherein the organic light-emitting unit comprises the organometallic compound described in any one of items 1 to 12 of the patent application scope.

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